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Artículos de revistas sobre el tema "Isoxazolones"

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Publicado: 10 de marzo de 2023

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1

Ang, Kiah H., Matthew Cox, Warren D. Lawrance, Rolf Prager, Jason A. Smith y Warren Staker. "Triplet Lifetimes, Solvent, and Intramolecular Capture of Isoxazolones". Australian Journal of Chemistry 57, n.º 1 (2004): 101. http://dx.doi.org/10.1071/ch03140.

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The first step in the photochemical decarboxylation of isoxazolones is the formation of the triplet state of the isoxazolone. We present evidence for the first time from flash laser photolysis of the lifetime of such species, and examples of their capture by solvent and by intramolecular cycloaddition.
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2

Cox, Matthew, Saba Jahangiri, Michael V. Perkins y Rolf H. Prager. "Some Synthetic Approaches to Glutamate AMPA Receptor Agonists Based on Isoxazolones". Australian Journal of Chemistry 57, n.º 7 (2004): 685. http://dx.doi.org/10.1071/ch04041.

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Several approaches to the synthesis of derivatives of the antifungal antibiotic TAN-950A, which is also an agonist of glutamate at hippocampal neurons, are reported. Additions of isoxazolon-4-yl anions to methyleneoxazolidinones were not useful because addition occurred predominantly through N-2. Similarly addition of the isoxazolon-4-yl radicals to model Michael acceptors occurred predominantly through N-2. Racemic analogues of TAN-950A were prepared by reaction of isoxazolone Mannich bases with acetylaminomalonate or addition of β-ketoester anions to dehydroalanines. The best approach to enantiomerically pure analogues was by acylation of pyroglutamates, followed by reaction with hydroxylamine.
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3

Reddy, Koduru Janardhan y Kap Duk Lee. "Separation Studies of Pd(II) from Acidic Chloride Solutions of Pt(IV), Ni(II) and Rh(III) by Using 4-Aroyl-3-Phenyl-5-Isoxazolones". E-Journal of Chemistry 9, n.º 2 (2012): 756–65. http://dx.doi.org/10.1155/2012/802621.

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This study examined the effect influence of various factors on the extraction of Pd(II) to develop a new liquid-liquid extraction mechanism for the selective separation of palladium(II) from its acidic chloride solutions using 4-aroyl-3-phenyl-5-isoxazolones (HA), such as 3-phenyl-4-(4-fluorobenzoyl)-5- isoxazolone (HFBPI), 3-phenyl-4-benzoyl-5-isoxazolone (HPBI) and 3-phenyl-4- (4-toluoyl)-5-isoxazolone (HTPI). The extraction strength of Pd(II) with HA were in the following order: HFBPI > HPBI > HTPI, which is opposite to that observed with their pKavalues. HPBI was used to separate Pd(II) from Pt(IV), Ni(II) and Rh(III) metal ions and calculated their separation factors (S.F.) were followed in the order: Pd/Ni (40±0.4) > Pd/Pt (25±0.2) > Pd/Rh (15±0.3 > Rh/Ni (2.7±0.3) > Pt/Ni ≈ Rh/Pt (1.7±0.2). The loading and striping of Pd(II) (1.12×10-4mol L-1) were also examined using 1.0×10-3mol L-1HPBI in CHCl3and 1.0 mol L-1HCl, respectively. The results demonstrated that the maximum (97.5%) extraction and desorption (89%) of metal required at least 3.0 cycles. The developed method was applied successfully to the separation of palladium from synthetic water samples.
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4

Ciura, Krzesimir, Joanna Fedorowicz, Hanna Kapica, Monika Pastewska, Wiesław Sawicki y Jarosław Sączewski. "Interaction between Antifungal Isoxazolo[3,4-b]Pyridin 3(1H)-One Derivatives and Human Serum Proteins Analyzed with Biomimetic Chromatography and QSAR Approach". Processes 9, n.º 3 (12 de marzo de 2021): 512. http://dx.doi.org/10.3390/pr9030512.

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The development of effective, nontoxic antifungal agents is one of the most important challenges for medicinal chemistry. A series of isoxazolo [3,4-b]pyridine-3(1H)-one derivatives previously synthesized in our laboratory demonstrated promising antifungal properties. The main goal of this study was to investigate their retention behavior in a human serum proteins-high-performance liquid chromatography (HSA-HPLC) system and explore the molecular mechanism of HSA-isoxazolone interactions using a quantitative structure–retention relationship (QSRR) approach. In order to realize this goal, multiple linear regression (MLR) modeling has been performed. The proposed QSRR models presented correlation between experimentally determined lipophilicity and computational theoretical molecular descriptors derived from Dragon 7.0 (Talete, Milan, Italy) software on the affinity of isoxazolones to HSA. The calculated plasma protein binding (PreADMET software) as well as chromatographic lipophilicity (logkw) and phospholipophilicity (CHIIAM) parameters were statistically evaluated in relation to the determined experimental HAS affinities (logkHSA). The proposed model met the Tropsha et al. criteria R2 > 0.6 and Q2 > 0.5 These results indicate that the obtained model can be useful in the prediction of an affinity to HSA for isoxazolone derivatives and they can be considered as an attractive alternative to HSA-HPLC experiments.
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5

Rong, Wei, Tian Zhang, Ting Li y Juan Li. "Theoretical study of rhodium- and cobalt-catalyzed decarboxylative transformations of isoxazolones: origin of product selectivity". Organic Chemistry Frontiers 8, n.º 6 (2021): 1257–66. http://dx.doi.org/10.1039/d0qo01498b.

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6

Bustos, Carlos, Elies Molins, Juan-Guillermo Cárcamo, Marcelo N. Aguilar, Christian Sánchez, Ignacio Moreno-Villoslada, Hiroyuki Nishide, Ximena Zarate y Eduardo Schott. "A family of substituted hydrazonoisoxazolones with potential biological properties". New Journal of Chemistry 40, n.º 3 (2016): 2156–67. http://dx.doi.org/10.1039/c5nj02604k.

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7

Ebrahimlo, Ali Reza Molla, Jabbar Khalafy y Rolf H. Prager. "The Synthesis of Potential DNA Intercalators. 2. Tri- and Tetra-Cyclic Heterocycles". Australian Journal of Chemistry 62, n.º 2 (2009): 126. http://dx.doi.org/10.1071/ch08370.

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The reaction of 1,4-dichlorophthalazine and 2,3-dichloroquinoxaline with some isoxazolones gave their mono- and bis-isoxazolinyl derivatives. The base-catalyzed rearrangement of these derivatives afforded the corresponding tri- and tetracyclic heterocycles.
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8

Wentrup, Curt, Maria Wiedenstritt y Hans-Wilhelm Winter. "Acetylenes from Aldehydes. Preparation of Ethynylphenols and Phenylacetylenes by Flash Vacuum Pyrolysis of Isoxazolones". Australian Journal of Chemistry 68, n.º 8 (2015): 1233. http://dx.doi.org/10.1071/ch15234.

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The flash vacuum pyrolysis method of synthesis of acetylenes from aldehydes via isoxazolones is a convenient method for the preparation of a variety of derivatives, including kinetically unstable, sensitive compounds such as the ethynylphenols.
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9

Mahalanabis, Kumar K., S. K. Dutta Chowdhury, Mili Sarkar y Manisha Misra. "Synthesis of substituted isoxazolones and isoxazoles from cyanoenaminones". Journal of Chemical Research 2006, n.º 2 (1 de febrero de 2006): 78–80. http://dx.doi.org/10.3184/030823406776330864.

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10

Beccalli, Egle M., Tiziana Benincori y Alessandro Marchesini. "1,3-Oxazin-6-ones from 5(2H)-Isoxazolones". Synthesis 1988, n.º 08 (1988): 630–31. http://dx.doi.org/10.1055/s-1988-27660.

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11

De Castro, Pedro P., Juliana A. Dos Santos, Marcelo M. De Siqueira, Gabriel M. F. Batista, Hélio F. Dos Santos y Giovanni W. Amarante. "Quantum Chemical-Guided Steglich Rearrangement of Azlactones and Isoxazolones". Journal of Organic Chemistry 84, n.º 19 (16 de septiembre de 2019): 12573–82. http://dx.doi.org/10.1021/acs.joc.9b02099.

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12

Koch, Rainer, Hans-Joachim Wollweber, Hans Müller-Starke y Curt Wentrup. "α-Oxo-Iminoxyls of Isoxazolones, Pyrazol­ones and 1,2,3-Triazolone". European Journal of Organic Chemistry 2015, n.º 23 (15 de julio de 2015): 5143–49. http://dx.doi.org/10.1002/ejoc.201500728.

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13

Ciura, Krzesimir, Joanna Fedorowicz, Petar Žuvela, Mario Lovrić, Hanna Kapica, Paweł Baranowski, Wiesław Sawicki, Ming Wah Wong y Jarosław Sączewski. "Affinity of Antifungal Isoxazolo[3,4-b]pyridine-3(1H)-Ones to Phospholipids in Immobilized Artificial Membrane (IAM) Chromatography". Molecules 25, n.º 20 (20 de octubre de 2020): 4835. http://dx.doi.org/10.3390/molecules25204835.

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Currently, rapid evaluation of the physicochemical parameters of drug candidates, such as lipophilicity, is in high demand owing to it enabling the approximation of the processes of absorption, distribution, metabolism, and elimination. Although the lipophilicity of drug candidates is determined using the shake flash method (n-octanol/water system) or reversed phase liquid chromatography (RP-LC), more biosimilar alternatives to classical lipophilicity measurement are currently available. One of the alternatives is immobilized artificial membrane (IAM) chromatography. The present study is a continuation of our research focused on physiochemical characterization of biologically active derivatives of isoxazolo[3,4-b]pyridine-3(1H)-ones. The main goal of this study was to assess the affinity of isoxazolones to phospholipids using IAM chromatography and compare it with the lipophilicity parameters established by reversed phase chromatography. Quantitative structure–retention relationship (QSRR) modeling of IAM retention using differential evolution coupled with partial least squares (DE-PLS) regression was performed. The results indicate that in the studied group of structurally related isoxazolone derivatives, discrepancies occur between the retention under IAM and RP-LC conditions. Although some correlation between these two chromatographic methods can be found, lipophilicity does not fully explain the affinities of the investigated molecules to phospholipids. QSRR analysis also shows common factors that contribute to retention under IAM and RP-LC conditions. In this context, the significant influences of WHIM and GETAWAY descriptors in all the obtained models should be highlighted.
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14

Ang, KH, RH Prager y CM Williams. "The Chemistry of 5-Oxodihydroisoxazoles. XII. Trapping of Derived Ketenimines With Lithium Amides and Alkyllithiums". Australian Journal of Chemistry 48, n.º 1 (1995): 55. http://dx.doi.org/10.1071/ch9950055.

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Isoxazolones unsubstituted at C3 react with lithium amides or alkyllithiums to give ketenimines . The presence of an ethoxycarbonyl group at C4 allows capture of this species by addition of a second equivalent of the lithiated species to give enolates which can be alkylated in situ. The presence of a phenyl group at C4 gives a ketenimine which reacts intramolecularly in the presence of lithium amides, whereas alkyllithiums undergo addition in synthetically useful processes.
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15

CHANDE, M. S. y R. M. JOSHI. "ChemInform Abstract: Synthesis of Fused Thiazolo(5,4-d)isoxazoles and a Novel Rearrangement Involving Conversion of 5(4H)-Isoxazolones to 4(5H)-Isoxazolones." ChemInform 28, n.º 40 (3 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199740155.

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16

Kvaskoff, David y Curt Wentrup. "Thioketenes and Iminopropadienethiones RN=C=C=C=S from Isoxazolones". Australian Journal of Chemistry 63, n.º 12 (2010): 1694. http://dx.doi.org/10.1071/ch10340.

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Isoxazolones 6 undergo thermal elimination of propene and isopropylthiol to produce thioketenes 7 at 500–600°C under flash vacuum thermolysis conditions. At 700–900°C further fragmentation occurs to produce iminopropadienethiones, RNCCCS 8. In addition, 3-alkylisoxazolones 6d–e rearrange to cyanothioketenes 10d–e. Compounds 7, 8, and 10 were characterized by Ar matrix IR spectroscopy and comparison with density functional theory-calculated spectra. Thioketenes 7 reacted with amines to afford thioamides 11. Reaction of aryliminopropadienethiones 8 with amines caused cyclization to 2-aminoquinoline-4(1H)-thiones 16.
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17

Cox, Matthew, Fariba Heidarizadeh y Rolf H. Prager. "Flash vacuum pyrolysis of N-alkenylbenzotriazoles and N-alkenylisoxazolones". Australian Journal of Chemistry 53, n.º 8 (2000): 665. http://dx.doi.org/10.1071/ch00098.

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The flash vacuum pyrolysis of 1-(2-ethoxycarbonylethenyl)benzotriazole has been reinvestigated, and the processes leading to the formation of ethyl indole-3-carboxylate and 2-ethoxyquinolin-4(1H)-one elucidated. Similar pathways are followed in the flash vacuum pyrolysis of the corresponding benzisoxazolone. Some N-ethenylisoxazolones have been pyrolysed to form pyrroles, but rearrangement of the intermediate carbenes may be observed. Photolysis of the isoxazolones gives carbenes that may be captured by solvent or give pyrroles.
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18

Mazimba, Ofentse, Kabo Wale, Daniel Loeto y Tebogo Kwape. "Antioxidant and antimicrobial studies on fused-ring pyrazolones and isoxazolones". Bioorganic & Medicinal Chemistry 22, n.º 23 (diciembre de 2014): 6564–69. http://dx.doi.org/10.1016/j.bmc.2014.10.015.

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19

Batra, Sanjay, Mohammad Shamim Akhtar, Manju Seth y Amiya Prasad Bhaduri. "Chemistry of 5(2H)-isoxazolones: Novel conversion of positional isomers". Journal of Heterocyclic Chemistry 27, n.º 2 (febrero de 1990): 337–42. http://dx.doi.org/10.1002/jhet.5570270242.

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20

Beccalli, Egle M., Alessandro Marchesini y Tullio Pilati. "Synthesis of heterocyclic ketene N,O-acetals from 5(2H)-isoxazolones". Tetrahedron 53, n.º 30 (julio de 1997): 10433–40. http://dx.doi.org/10.1016/s0040-4020(97)00654-6.

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21

Flores, Alex F. C., Nilo Zanatta, Adriano Rosa, Sergio Brondani y Marcos A. P. Martins. "Synthesis of hydroxypyrazoles and 1-methyl-3-isoxazolones via haloform reactions". Tetrahedron Letters 43, n.º 28 (julio de 2002): 5005–8. http://dx.doi.org/10.1016/s0040-4039(02)00874-2.

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22

NAKAMURA, Koki, Keizo KOYA y Kozo SATO. "Single electron transfer-triggered ring opening reaction of isoxazolones and its application." Journal of Synthetic Organic Chemistry, Japan 47, n.º 7 (1989): 629–35. http://dx.doi.org/10.5059/yukigoseikyokaishi.47.629.

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23

August, Julie, Klaus Klemm, Harold W. Kroto y David R. M. Walton. "F.t.i.r. study of ynamines and ketenimines produced by thermolysis of substituted isoxazolones". Journal of the Chemical Society, Perkin Transactions 2, n.º 11 (1989): 1841. http://dx.doi.org/10.1039/p29890001841.

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24

BATRA, S. y A. P. BHADURI. "ChemInform Abstract: An Account of the Chemistry of 3,4-Disubstituted 5-Isoxazolones". ChemInform 26, n.º 36 (17 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199536302.

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25

ODASHIMA, Tsugikatsu, Seiichi SATOH, Tsugio SATO y Hajime ISHII. "SOLVENT EXTRACTION OF SOME TERVALENT LANTHANOIDS WITH 4-ACYL-3-PHENYL-5-ISOXAZOLONES". Solvent Extraction and Ion Exchange 13, n.º 5 (agosto de 1995): 845–54. http://dx.doi.org/10.1080/07366299508918306.

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26

Rageh, H. M., S. A. Ibrahim, M. A. Selim y H. M. Alsoghier. "Spectroscopic and semiempirical investigation of the structural features of hetarylazo-5-isoxazolones tautomerism". Journal of Saudi Chemical Society 21 (enero de 2017): S467—S474. http://dx.doi.org/10.1016/j.jscs.2015.01.007.

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27

Clerici, Francesca, Emanuela Erba, Pierluigi Mornatti y Pasqualina Trimarco. "Cycloaddition Reactions of 3-Methyloxazolium-5-olates to 4-Arylidene-5(4H)-isoxazolones". Chemische Berichte 122, n.º 2 (febrero de 1989): 295–300. http://dx.doi.org/10.1002/cber.19891220215.

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28

Flores, Alex F. C., Nilo Zanatta, Adriano Rosa, Sergio Brondani y Marcos A. P. Martins. "ChemInform Abstract: Synthesis of Hydroxypyrazoles and 1-Methyl-3-isoxazolones via Haloform Reactions." ChemInform 33, n.º 41 (19 de mayo de 2010): no. http://dx.doi.org/10.1002/chin.200241121.

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29

BECCALLI, E. M., A. MARCHESINI y T. PILATI. "ChemInform Abstract: Synthesis of Heterocyclic Ketene N,O-Acetals from 5(2H)-Isoxazolones." ChemInform 28, n.º 48 (2 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199748049.

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30

Ebrahimlo, Ali Reza Molla, Jabbar Khalafy, Ahmad Poursattar Marjani y Rolf H. Prager. "The synthesis of potential DNA intercalators. 3†. Triazanaphthalene, tetraaza anthracene and phenanthrene from isoxazolones". Arkivoc 2009, n.º 12 (19 de septiembre de 2009): 17–30. http://dx.doi.org/10.3998/ark.5550190.0010.c03.

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31

Christodoulou, Michael S., Sabrina Giofrè, Egle M. Beccalli, Francesca Foschi y Gianluigi Broggini. "Divergent Conversion of 4-Naphthoquinone-substituted 4H-Isoxazolones to Different Benzo-fused Indole Derivatives". Organic Letters 22, n.º 7 (17 de marzo de 2020): 2735–39. http://dx.doi.org/10.1021/acs.orglett.0c00709.

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32

Jiang, Di, Zheng Xue, Yongjun Li, Huibiao Liu y Wensheng Yang. "Synthesis of donor–acceptor molecules based on isoxazolones for investigation of their nonlinear optical properties". Journal of Materials Chemistry C 1, n.º 36 (2013): 5694. http://dx.doi.org/10.1039/c3tc31228c.

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33

Yu, Wei, Zhengang Liu, Bing Han, Qiang Liu, Wei Zhang, Li Yang y Zhong-Li Liu. "Selective Reduction of the Exocyclic Double Bond of Isoxazolones and Pyrazolones by Hantzsch 1,4-Dihydropyridine". Synlett 2005, n.º 10 (7 de junio de 2005): 1579–80. http://dx.doi.org/10.1055/s-2005-869860.

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34

Chans, Guillermo M., Elizabeth L. Moyano y Gloria I. Yranzo. "Novel Synthesis of 2-thienylcarbonyl-cyclohexane-1,3-dione as Building Block for Indazolones and Isoxazolones". Australian Journal of Chemistry 64, n.º 5 (2011): 638. http://dx.doi.org/10.1071/ch11015.

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A new synthetic methodology using ultrasonic treatment was applied to the C-acylation of 1,3-cyclohexanedione with thiophene-2-carbonyl chloride to afford 3-hydroxy-2-(2-thienylcarbonyl)cyclohex-2-en-1-one (5). This compound was used as a building block to prepare different bicyclic systems: tetrahydro-4H-indazol-4-ones (7a–c and 9a,b,d), and 6,7-dihydrobenzisoxazole (11) by reaction with different hydrazines and hydroxylamine, respectively. Structural elucidation of all compounds was thoroughly achieved by NMR spectroscopy.
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35

Giovannoni, Maria Paola, Letizia Crocetti, Niccolò Cantini, Gabriella Guerrini, Claudia Vergelli, Antonella Iacovone, Elisabetta Teodori et al. "New 3‐unsubstituted isoxazolones as potent human neutrophil elastase inhibitors: Synthesis and molecular dynamic simulation". Drug Development Research 81, n.º 3 (4 de diciembre de 2019): 338–49. http://dx.doi.org/10.1002/ddr.21625.

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36

RAO, M. H., A. P. R. REDDY y V. VEERANAGAIAH. "ChemInform Abstract: A Convenient Approach to the Synthesis of Quinoxalines from Isoxazolones and 1,2-Diaminobenzenes." ChemInform 23, n.º 17 (22 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199217200.

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37

Gammill, Ronald B., Sharon A. Nash, Larry T. Bell y William Watt. "The synthesis and chemistry of functionalized furochromones.4.1 Addition of nitronate anions to 30bromochromone and 6-bromofurochromone. An expedient route to furo(3′,2′:6,7)-benzopyrano(2,3-d)-isoxazolones and chromono(2,3-d)isoxazolones." Tetrahedron Letters 33, n.º 8 (febrero de 1992): 993–96. http://dx.doi.org/10.1016/s0040-4039(00)91842-2.

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38

Sekily, Mohamed A. El. "Studies on dehydro-D-erythro-ascorbic acid 2-arylhydrazone 3-oximes: conversion into substituted triazoles and isoxazolones". Journal of Chemical Research 2006, n.º 12 (1 de diciembre de 2006): 771–73. http://dx.doi.org/10.3184/030823406780199785.

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39

Valduga, Claudete J., Denise B. Santis, Hugo S. Braibante y Mara E. F. Braibante. "Reactivity ofp-phenyl substituted β-Enamino compounds using K-10/ultrasound.II. Synthesis of isoxazoles and 5-Isoxazolones". Journal of Heterocyclic Chemistry 36, n.º 2 (marzo de 1999): 505–8. http://dx.doi.org/10.1002/jhet.5570360229.

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40

Gerace, Alessandro, Valentina Masini, Letizia Crocetti, Maria Paola Giovannoni y Marta Ferraroni. "X-ray structural study of human neutrophil elastase inhibition with a series of azaindoles, azaindazoles and isoxazolones". Journal of Molecular Structure 1274 (febrero de 2023): 134595. http://dx.doi.org/10.1016/j.molstruc.2022.134595.

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41

Kadam, Hari K., Komal Salkar, Akshata P. Naik, Milind M. Naik, Lalitprabha N. Salgaonkar, Lakshangy Charya, Kathleen C. Pinto, Vinod K. Mandrekar y Teotone Vaz. "Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens". ChemistrySelect 6, n.º 42 (10 de noviembre de 2021): 11718–28. http://dx.doi.org/10.1002/slct.202101798.

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42

Beccalli, Egle M., Alessandro Marchesini y Tullio Pilati. "2-acyl-2,3-dihydro-1,3-oxazin-6-ones and pyrrolo[l,2-a]pyrimidines from 5(2h)-isoxazolones". Tetrahedron 44, n.º 19 (enero de 1988): 6225–34. http://dx.doi.org/10.1016/s0040-4020(01)89813-6.

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43

Canonne, P., D. Thibeault y G. Fytas. "Etude des reactions du di(bromomagnesio)-1,4 butane et du di(bromomagnesio)-1,5 pentane sur les isoxazolones-5 encombrees". Tetrahedron 42, n.º 15 (enero de 1986): 4203–10. http://dx.doi.org/10.1016/s0040-4020(01)87644-4.

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44

Buonomenna, M. G., R. Molinari y E. Drioli. "Selective mass transfer of iron(III) in supported liquid membrane using highly acidic extractants, 3-phenyl-4-acyl-5-isoxazolones". Desalination 148, n.º 1-3 (septiembre de 2002): 257–62. http://dx.doi.org/10.1016/s0011-9164(02)00707-5.

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45

BATRA, S., M. SETH y A. P. BHADURI. "ChemInform Abstract: Lithium Aluminum Hydride Induced Ring Contraction of 5(2H)- Isoxazolones to Aziridines: Prediction of the Stereochemistry of Products". ChemInform 23, n.º 21 (22 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199221095.

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46

Ciura, Krzesimir, Joanna Fedorowicz, Filip Andrić, Petar Žuvela, Katarzyna Ewa Greber, Paweł Baranowski, Piotr Kawczak, Joanna Nowakowska, Tomasz Bączek y Jarosław Sączewski. "Lipophilicity Determination of Antifungal Isoxazolo[3,4-b]pyridin-3(1H)-ones and Their N1-Substituted Derivatives with Chromatographic and Computational Methods". Molecules 24, n.º 23 (26 de noviembre de 2019): 4311. http://dx.doi.org/10.3390/molecules24234311.

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The lipophilicity of a molecule is a well-recognized as a crucial physicochemical factor that conditions the biological activity of a drug candidate. This study was aimed to evaluate the lipophilicity of isoxazolo[3,4-b]pyridine-3(1H)-ones and their N1-substituted derivatives, which demonstrated pronounced antifungal activities. Several methods, including reversed-phase thin layer chromatography (RP-TLC), reversed phase high-performance liquid chromatography (RP-HPLC), and micellar electrokinetic chromatography (MEKC), were employed. Furthermore, the calculated logP values were estimated using various freely and commercially available software packages and online platforms, as well as density functional theory computations (DFT). Similarities and dissimilarities between the determined lipophilicity indices were assessed using several chemometric approaches. Principal component analysis (PCA) indicated that other features beside lipophilicity affect antifungal activities of the investigated derivatives. Quantitative-structure-retention-relationship (QSRR) analysis by means of genetic algorithm—partial least squares (GA-PLS)—was implemented to rationalize the link between the physicochemical descriptors and lipophilicity. Among the studied compounds, structure 16 should be considered as the best starting structure for further studies, since it demonstrated the lowest lipophilic character within the series while retaining biological activity. Sum of ranking differences (SRD) analysis indicated that the chromatographic approach, regardless of the technique employed, should be considered as the best approach for lipophilicity assessment of isoxazolones.
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47

Reddy, B. Ramachandra, J. Rajesh Kumar y A. Varada Reddy. "3-phenyl-4-acyl-5-isoxazolones as reagents for liquid-liquid extraction of tetravalent zirconium and hafnium from acidic chloride solutions". Journal of the Brazilian Chemical Society 17, n.º 4 (agosto de 2006): 780–84. http://dx.doi.org/10.1590/s0103-50532006000400021.

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48

Grigg, Ronald, M. Ruhul A. Sarkar, Abirami Thayaparan, Visuvanathar Sridharan y Colin W. G. Fishwick. "Pd(0) catalyzed three–five-component C-2-arylallylation of active methylene heterocycles: pyrazolones, oxazolones, isoxazolones and N,N′-dimethylbarbituric acid". Tetrahedron 63, n.º 30 (julio de 2007): 7213–28. http://dx.doi.org/10.1016/j.tet.2007.04.090.

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49

Ye, Zaijun, Lijuan Bai, Yan Bai, Zongjie Gan, Hui Zhou, Tao Pan, Yu Yu y Jing Zhou. "High diastereoselective synthesis of spiro-isoxazolonechromans via domino oxa-Michael/1,6-addition reactions of ortho-hydroxyphenylsubstituted para-quinone methides with unsaturated isoxazolones". Tetrahedron 75, n.º 5 (febrero de 2019): 682–87. http://dx.doi.org/10.1016/j.tet.2018.12.064.

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50

Valduga, Claudete J., Denise B. Santis, Hugo S. Braibante y Mara E. F. Braibante. "ChemInform Abstract: Reactivity of p-Phenyl Substituted β-Enamino Compounds Using K-10/Ultrasound. Part 2. Synthesis of Isoxazoles and 5-Isoxazolones." ChemInform 30, n.º 36 (13 de junio de 2010): no. http://dx.doi.org/10.1002/chin.199936147.

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